


Saturday night foursome

by ElleLouMay



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Angst, Double Penetration, First Kiss, First Time, Foursome - M/M/M/M, Gay Sex, M/M, Old Friends, Smut
Language: English
Status: Completed
Published: 2019-12-08
Updated: 2019-12-08
Packaged: 2021-02-25 22:33:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,293
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21723046
Author URL: https://archiveofourown.org/users/ElleLouMay/pseuds/ElleLouMay
Summary: Dean's two worlds collide when his colleague (Castiel) meets two of his college friends (Benny and Lee.)
Relationships: Benny Lafitte/Dean Winchester, Castiel/Dean Winchester, Leo Webb/Dean Winchester
Comments: 2
Kudos: 58





	Saturday night foursome

Dean looked forward to Saturdays because it meant he'd finally get a chance to kick back and relax, he'd head to Swayze's, shoot some pool, knock back some beers and finally ditch the tension from a week spent under the hoods of cars.

He loved his job but man it was really putting a strain on his body now that he'd reached the wrong side of thirty.

This particular Saturday was even better because for once he'd managed to get his old crowd from college to meet his new friend, though friend doesn't quite describe how Dean feels about Castiel Novak that's for sure.

When Dean gets to the bar Lee and Benny have already claimed themselves a booth and they're each well into what looks to be their second beers of the night.

Lee notices Dean first and his face breaks into a wide and genuine smile as he nudges Benny.

Dean slides into the booth, sitting opposite the pair, and chuckles as Benny flicks a sugar packet at Lee.

"Where's Ash?" Dean asks the two.

Benny sighs, "Bailed last minute, Cher."

"Crowley too, bud," Lee adds, shrugging, "I'm sure they'll meet whats-his-name some other time."

Benny smirks at Lee mockingly and rolls his eyes at Dean.

Ever since Dean mentioned Cas to his friends Lee has been acting like a kicked puppy and though Dean pretends he doesn't know why, he does know.

Lee always had a soft spot for him and though their college days were fun and Dean enjoyed the freedom hanging with Lee gave him he was never looking for more than friendship and experimentation from his best friend.

Although if Lee asked him to do some of the stuff they did again Dean would have a hard time saying n-

"Hello, Dean."

It would be comical how Dean's heart tries to jump out of his chest every time he hears Castiel saying his name (or just talking in general) if it wasn't just so damn tragic.

He can feel the blush burning his cheeks and he knows it's already spread to his ears judging by the way Benny is smirking at him.

He glares at Benny across the booth and forces a confidant and natural looking smile on to his face as he stands to greet Castiel, clapping him just once on the back before gesturing for him to sit in the seat that's...next...to...his...oh, god.

"Uhh, hey, Cas," Good job, Winchester, you sound like a lizard person trying to imitate human interaction, "Have a seat and I'll introduce you to the guys."

Castiel sits, looking stiff and out of place in the relaxed bar wearing his usual suit, tie and trench coat get up and looking like a massive dork.

It just makes Dean all the more enamoured with the guy.

"This here is Lee, he's cocky but you get used to him," Dean smiles genuinely at his friend and gets a warm one from Lee in response, "And this is Benny, he's a big softy and he cooks the best salt water cat fish I've ever eaten."

Benny laughs, deep and long, and Dean watches as both of his friends shake hands with Castiel.

It feels good to finally have his two worlds collide and he can tell by his friends expressions that they already feel more at ease now that Castiel is here in the flesh.

Benny gets a round in and Dean meets Lee's gaze.

There's something in his eyes, a hint of a look that Dean hasn't seen in a while that promises a whole world of trouble and pleasure combined.

It actually sends shivers down his spine when Lee flicks his gaze to Castiel instead, eyes growing hungry in a way that causes goosebumps to erupt across Dean's forearms.

Beside him Castiel gulps and Dean knows the instant their eyes meet because suddenly Castiel's hand is shooting out and gripping Dean's thigh in a hold that's almost painful.

Benny interrupts the strange exchange when he comes back to the table laden with beers and announces to the group that shots are up next round.

Dean spends the next ten minutes trying to silently ask Lee what he's thinking while he drinks slowly from his bottle but Lee is thoroughly distracted by a story Benny is telling Castiel about college, one they all lived through that never seems to get old.

"What was the brunette ones name, Dean?" Lee asks, the ghost of that same look from earlier dancing in his eyes.

For a moment Dean is confused, he wasn't really listening and now they seem to have changed to a different story and...oh! Dean knows what this certain story is now, "Lisa, she was a yoga instructor."

Lee laughs lightly and nudges Benny, "Dean always did have a thing for dark hair," Benny shakes his head but laughs a little too, "Anyway, it was me, Dean, Benny, Lisa and this chick called Tessa that didn't really get involved. I don't know who started it but-"

Dean cuts his friend off with a chuckle, "You did." 

Benny laughs again and Lee flips Dean off before continuing, "We were all a little drunk and honestly me and Dean had been hitting my bong for most of the day so we were just along for the ride. Lisa was pretty wild and she was a really kinky kinda girl too, wasn't she, Dean?"

"And bendy, don't forget bendy." Dean smiles indulgently at Lee.

"Oh yah, bendy too," Lee leans further over the table, gazing directly at Castiel, "She wanted to watch as I fucked Dean and Benny fucked me."

Dean sneaks a peak at Castiel's face and is startled when bright, blue, eyes meet his.

His pupils are blown so wide there's barely any trace of blue and he looks like he's restraining himself with all he's got, what he's restraining himself from Dean doesn't actually know but he can sure guess.

He suddenly feels too hot and he knows for a fact his skin is bright red.

"I gotta go use the restroom, fellas, be right back."

Castiel shuffles out of the booth so Dean can get out and Dean swears he can feel three pairs of eyes staring holes through his ass as he walks away, trying not to trip over any chair legs on the way.

•

Dean heads straight for the sink as soon as he gets inside and starts splashing his face with water, he feels like he's either going to die of a heart attack or cum in his pants...maybe he'll end up doing both.

He has no idea how long he stands in front of the mirror before the door swings open and Lee steps in.

Dean meets his gaze over his shoulder in the mirror and Lee smiles, a hungry smile that almost melts Dean's insides.

"I was thinkin'," Lee moves closer, approaching Dean like he's a scared animal, "Maybe we should have a repeat of Arizona."

Dean's mind pulls up vivid images and sensations that almost make his knees give out, he clutches the counter in a white knuckle hold.

"I don't have Lisa's number anymore." He tries to play it off with a laugh but it comes out wrong.

"I don't mean with Lisa, Dean." Lee is speaking right in his ear now, breath tickling the fine hairs there.

It's been so fucking long since he got laid.

Been so long since he bottomed.

"Tell me you want this." Lee murmurs against the shell of his ear.

Dean shudders, breaths shallow as he eyes Lee in the mirror.

"I'm too old, I don't look like I used to." It sounds feeble even to Dean's ears but the concerns are genuine enough.

Lee strokes his hand flat down from between Dean's shoulder blades to the small of his back, "That's a crock of shit and you know it, I'd love to fuck that tight ass of yours again and you'd better bet that smoking hot accountant is just gagging for the chance."

Dean feels his eyes roll slightly as his mind conjures the images and he sags a little against Lee, luckily Lee is more than capable of supporting Dean's weight.

"Say yes, Dean." Lee coaxes, his talented tongue flicking out to lap gently at the very edge of Dean's ear.

"Castiel wouldn't be up for it." He can't keep the pout off his face.

Lee chuckles, low and dark, "He already said yes, he left with Benny ten minutes ago. They're just waiting on you."

•

It seems Lee thought of everything, they end up going to his house which is bigger than Dean and Benny's and apparently Lee anticipated something like this happening because his large bedroom looks like the set of a porno.

Dean's seen Lee's bed once or twice before but it never had crimson, silk, sheets and soft looking restraints attached to the bedposts either of those times.

In the middle of the bed Benny is buck naked and propped up at the top, be grins wickedly and throws out a wink when Dean blushes.

"How long have you freaks been planning this?" Dean asks with a nervous laugh.

"Too long, Cher." Benny replies but it's obvious from his tone that he's joking.

Footsteps on hardwood announce Lee's approach and he's followed by Castiel, when Dean turns he almost faints because Castiel has removed everything except for his briefs and boy was he holding out.

That massive trench coat and ill fitting suit has been hiding a firmly muscled body and what looks like a pair of runners thighs.

Lee chuckles and draws Dean's attention back to him where he's deftly stripping himself out of his own clothes, revealing the body Dean knows every inch of to the hungry eyes of Benny, Castiel and Dean himself.

For a moment everyone seems to watch Lee and he makes a show of stripping slowly and with exaggerated sexiness.

Wide hands grip Dean's plaid button down and he spins in Castiel's hold as the other man begins removing his over shirt.

Dean lifts his arms when Castiel pulls at the bottom of his t-shirt and feels a second pair of hands teasing the skin of his back before he's being led backwards to the bed by Lee and Castiel.

Castiel pops the button on Dean's jeans and slides the zipper down with his teeth making Dean's dick twitch.

"Fuck, Dean." Lee gasps in a strangled voice as Castiel works Dean's jeans down over his ass.

Lee's fingers toy with the strip of satin and lace Dean is wearing low on his hips and he can hear Benny murmur out what sounds like 'Holy shit' behind him.

Castiel is staring at Dean's crotch in rapture and it's making him feel all kinds of hot under the collar.

Wide hands grip Dean under the arms and he's manhandled by Castiel until he's laying dead center on the wide bed with Lee on his right, Benny laying on his side on his left and Castiel sat on his right side down by his knees.

A beat passes and then they all seem to start at once.

Castiel grips Dean's thighs, one in each hand, and starts mouthing over the hard line of Dean's erection through his pink panties.

Benny mouths at Dean's neck, nipping and sucking hard enough to leave marks and making Dean arch up off of the bed.

And Lee captures Dean's mouth, closed lips at first with just a gentle brush of soft velvet until Dean is moaning as Lee flicks his tongue up into his mouth.

It's overwhelming and Dean feels like he's being torn into three as they all lavish his body with attention.

Benny has moved from his neck and is now sucking his nipples in sharp little pulls that are steadily driving Dean crazy.

Lee is raking his nails through his hair, tugging and pulling as he fucks Dean's mouth with all he's got.

Castiel is moaning like a damn pornstar as his saliva mixes with Dean's precum, soaking into the expensive material and ruining them forever.

Dean's hole twitches in time with his dick as Lee delves particularly deep with his skilled tongue and he's suffocating, gasping out pleas for more and more even though he knows Lee and Benny are fucking sadists and they're going to draw this out as long as possible.

Maybe Cas will take pity on him.

His voice is whiny as he moans out their names, not knowing exactly what he's asking for from each man but asking nonetheless.

Lee breaks apart and reaches into his bedside drawer, passing something down to Castiel without being asked, and then there's the distinct pop of a cap being opened and warm hands are tugging Dean's ruined panties to the side to expose his hole.

Benny pushes a small throw pillow under the small of Dean's back, manhandling him into position like Castiel did earlier, and then there's the too cold sensation of lube smearing around his ass and Dean is trembling and keening like a virgin.

Lee pulls Dean's hand off of the sheets where he was gripping on for dear life and threads their fingers together, they gaze at each other briefly until Dean throws his head back and groans.

Castiel is slowly breaching his hole with one of this thick fingers and the delicious stretch is so much more than Dean can handle.

"Beautiful." Benny says in awe.

Castiel is past the first knuckle now and he drags his finger out slowly before plunging in further the second time, punching another desperate noise out of Dean.

"So responsive." Lee whispers, sounding wrecked already.

A second finger joins the first and Castiel plunges so deep, curling his fingers and managing to find Dean's prostate on the first try.

Dean curls up off the bed, back bowing and eyes rolling.

Castiel starts scissoring his fingers inside Dean as Benny bends to swallow the sounds Dean is making.

Benny was always a phenomenal kisser, probably even better than Lee, but right now Dean can't even focus on breathing let alone kissing so he's pretty lacking in the lip locking.

Benny doesn't seem to mind, he's doing the majority of the work, sliding his tongue against Dean's as his fingers pinch each of Dean's nipples.

He's not sure how much more he can take, he already feels like he's about to blow his load any second and he's honestly surprised he hasn't already.

But then Lee has to go and make it worse.

"Dean?" Lee asks, directly in his ear.

Dean groans incoherently in reply as Castiel thrusts three fingers in and out.

"Do you think you'd be up for double penetration tonight?"

Castiel mouths at one of Dean's balls as he relentlessly finger fucks his hole.

Dean all out screams his reply and then he's being pulled and pushed again, lifted and positioned, like putty.

He's on his hands and knees, struggling to hold himself up, with Castiel beneath him looking like a sex god.

A gentle hand rubs over his ass as Lee positions himself behind Dean, hands running along the plains of his back before settling on his waist.

He can hear the click of that cap opening again and Lee shudders against him with a harsh intake of breath that quickly turns into a drawn out moan.

Dean figures Benny is taking up the rear, so to speak.

"Are you okay, Dean?" Castiel asks, staring directly into his soul.

Dean tries to smile but he's dazed and half out of his mind with how horny he is, "Yeah, Cas."

Castiel gives him a look like he's about to devour him before looking over Dean's shoulder at Lee.

There's no warning before Castiel is pushing his lube slick cock against Dean's hole and it's so fucking big, it's huge, fuck.

He feels like it's going to split him in two and how on Earth is Lee gonna fit too? Lee isn't exactly small. None of them are.

Castiel groans deep, the sound almost a growl, as his cock drags inside Dean.

He must be wearing a ribbed condom because Dean can feel tiny ridges and bumps.

Somewhere behind Dean can hear Benny fucking Lee hard and fast while Lee curses and shouts praises.

"Oh fuck, Benny, fuck, if you don't stop I'm gonna cum!" 

Castiel huffs out a breaththless laugh that melds into a loud moan as he finally bottoms out, Dean echoes the sound and grinds down a little against Cas.

He feels powerful and powerless all at the same time, like he's insane with how badly he wants this.

"Cas…" Dean hears himself whimper, arms and legs shaking with the effort if holding himself up.

"Shh, shh, I know, you're doing so good for us, Dean." Castiel breaths in response, sounding like he's barely keeping it together.

"Fuck him, Castiel." Benny reached over and punctuates his words with a firm slap to Dean's ass.

His hole tightens around Cas' cock on impact causing Cas to moan louder than before and then he's pulling out, almost all the way, and pounding harshly back in.

Dean sees stars bursting in front of his eyes and he's higher than he's ever been on any drug he's tried before.

He couldn't stop the sounds he's making if he tried and he knows how much it's affecting all of them when he hears Lee swearing and moaning Dean's name as Benny and Cas echo his shout.

Cas gets in a good dozen thrusts and Dean is so damn close to cumming until Cas pulls nearly fully out and when he plunges back in its suddenly so much more.

And Dean is vibrating out of his skin as Lee alternates his thrusts with Cas making sure Dean is always full.

For a while Dean is deaf and blind to everything around him, lost to the throbbing tingle shooting up his spine from the inside and the white fuzz filling his skull but then he comes back to himself and hears the absolute chaos of noise in the room.

Castiel is grunting and growling as he fucks hard and fast up into Dean.

Lee is slightly higher pitched, hands clawing at Dean's back as he slams into him from behind like a man possessed.

Benny is positively roaring as he sings praise to Lee and to Dean, the sound of skin slapping is a constant background.

Castiel uses one hand at the back of Dean's head to pull him down into an all consuming kiss that lights fireworks behind his eyelids and makes the marrow in his bones pulse in time to the beating of his heart and then Dean is cumming.

Thick, white, ropes coating Castiel's chest and neck in a sticky mess that Dean collapses into.

The world goes black.

When Dean returns to himself Castiel is gripping his upper arms as his cock jerks and throbs inside his ass and Lee is stiff as a board behind him, fingers gripping Dean's hipbones hard enough to leave bruises.

Benny has the sense to seperate Lee from Dean before he can slump forwards and when they lay out next to Dean and Cas Lee is twitching with his mouth slack and his cheeks stained pink.

Benny chuckles and runs a hand down Lee's flank, "I think I fucked his brains out."

Castiel laughs loudly, a musical sound that echoes inside his chest and shakes through Dean.

"We are so doing this again." Lee sounds beyond fucked out.

"I would be amenable to that." Cas sobers up, trailing his fingers lazily through Dean's hair.

"I'm in if you are, Cher?" Benny flicks Dean's shoulder.

"Hell yeah."


End file.
